So had the pleasure of sailing this saturday and what do you know I rip the hook out of my hobie 18 comp tip....... I just bought this thing about this time last year and kinda dissapointed. Any idea how hard the repair is going to be to fix this? The fiberglass has peeled back in an area the size of the hook and some glass is missing. "Think Chipping plastic". I was thinking about getting some west system and the High density filler and smearing it like a putty as much as I can get into it then though bolting at least the 3 bolts that will go through the widest portion of the tip.

Do not just smear putty in there, you will be wasting your time. You need to pull out the head cap. The rivets that hold the hook on pass through the fiberglass comptip and into the aluminum head cap. The head cap acts as a backing for the rivets to pull against. One guess would be that salt water got into the head cap and the stainless rivets corroded the holes in the head cap and then the rivets pulled through. Or possibly the rivets simply weren't pulled properly from the factory. In any case, you need to get the head cap out, do a little investigation, and repair properly. If fiberglass has been peeled off of the comptip, then you need to replace that fiberglass. If the holes in the head cap have become oversized, then your best bet may be to replace the head cap.